Discovery of Oxygen Induced Chemoselectivity in Pd-Catalyzed C-H Functionalization: Cross-Dehydrogenative Coupling vs C-H Amination

被引：5

作者：

Ann Babu, Sheba ^{[1
,2
]}

Varughese, Sunil ^{[1
,2
]}

Mathew, Jomon ^{[3
]}

John, Jubi ^{[1
,2
]}

机构：

[1] Natl Inst Interdisciplinary Sci & Technol NIIST, Chem Sci & Technol Div, CSIR, Thiruvananthapuram 695019, India

[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India

[3] St Josephs Coll Autonomous, Res & Postgrad Dept Chem, Calicut 673008, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 14期

关键词：

AEROBIC OXIDATIVE AMINATION; TRANSIENT DIRECTING GROUPS; MOLECULAR-OXYGEN; BOND FORMATION; ORTHO-OLEFINATION; C(SP(3))-H BONDS; PALLADIUM; ACTIVATION; DERIVATIVES; CARBAZOLES;

D O I：

10.1021/acs.joc.3c00651

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have come across a substrate namely, 5-benzoyl-pyrrolo[2,1-a]isoquinoline in which three different functionalizableC-H bonds were identified that could be judiciously transformedsite selectively for the generation of complex polyring fused N-heterocycles. A Pd-catalyzed cross-dehydrogenative couplingof 5-benzoyl-pyrrolo[2,1-a]isoquinoline afforded8H-indeno-pyrrolo[2,1-a]isoquinolinoneand an oxygen induced palladium catalyzed selective C-H aminationin the same substrate provided a pentacene viz., 9H-indolo-pyrrolo[2,1-a]isoquinoline. We also observedthe formation of a multiring fused benzazepine scaffold by the siteselective C-H amination in 5-(4-nitro benzoyl)-pyrrolo[2,1-a]isoquinoline.

引用

页码：9877 / 9892

页数：16

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